NP-MRD: Showing NP-Card for 27-Deoxy-5beta-cyprinol (NP0086733)

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Record Information

Version

2.0

Created at

2022-05-11 16:29:29 UTC

Updated at

2022-05-11 16:29:29 UTC

NP-MRD ID

NP0086733

Secondary Accession Numbers

None

Natural Product Identification

Common Name

27-Deoxy-5beta-cyprinol

Description

27-Deoxy-5b-cyprinol, also known as 5-CTTL, belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. Thus, 27-deoxy-5b-cyprinol is considered to be a bile acid lipid molecule. 27-Deoxy-5b-cyprinol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 27-deoxy-5b-cyprinol participates in a number of enzymatic reactions. In particular, 27-deoxy-5b-cyprinol can be biosynthesized from 5-b-cholestane-3a ,7a ,12a-triol through the action of the enzyme sterol 26-hydroxylase, mitochondrial. In addition, 27-deoxy-5b-cyprinol can be converted into 3a,7a,12a-trihydroxy-5b-cholestan-26-al through its interaction with the enzyme sterol 26-hydroxylase, mitochondrial. 27-Deoxy-5beta-cyprinol is found in Apis cerana. In humans, 27-deoxy-5b-cyprinol is involved in cerebrotendinous xanthomatosis (ctx).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02231219002D          

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M  END

     RDKit          3D

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M  END

  Mrv0541 02231219002D          

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   12.2808  -18.1049    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5406  -21.3732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9696  -18.9038    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7700  -20.1312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2551  -20.1357    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 12 27  1  1  0  0  0
 13 28  1  6  0  0  0
  5 29  1  1  0  0  0
  2 30  1  6  0  0  0
  8 31  1  6  0  0  0
 17 32  1  6  0  0  0
  4 33  1  1  0  0  0
  9 34  1  1  0  0  0
 11 35  1  6  0  0  0
 10 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0086733

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C27H48O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h16-25,28-31H,5-15H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
XJZGNVBLVFOSKJ-XZULNKEGSA-N

> <FORMULA>
C27H48O4

> <MOLECULAR_WEIGHT>
436.6676

> <EXACT_MASS>
436.355260024

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
53.375276321490546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
3.620167761333334

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.2963399055959

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.41832287471465

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1481999506883772

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
124.72619999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-cttl

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      13.275 -36.822   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.275 -38.362   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.609 -39.132   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.942 -38.362   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.942 -36.822   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.609 -36.052   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.276 -39.132   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.610 -38.362   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.610 -36.822   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.276 -36.052   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.944 -36.052   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.944 -34.512   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.610 -33.742   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.276 -34.512   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.408 -36.528   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.314 -35.282   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.408 -34.036   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.883 -32.576   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.856 -31.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.384 -32.257   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.411 -33.398   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.912 -33.079   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.939 -34.219   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.440 -33.900   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      26.465 -35.679   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      29.467 -35.041   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      20.104 -32.985   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.610 -32.207   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.942 -35.287   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.946 -39.129   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      19.939 -39.129   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0      22.924 -33.796   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      15.942 -39.897   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      18.610 -35.287   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      20.104 -37.578   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      17.276 -37.587   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   33                                             
CONECT    5    4    6   10   29                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10   11   34                                             
CONECT   10    9    5   14   36                                             
CONECT   11    9   12   15   35                                             
CONECT   12   11   13   17   27                                             
CONECT   13   12   14   28                                                  
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18   32                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   26                                                       
CONECT   25   23                                                            
CONECT   26   24                                                            
CONECT   27   12                                                            
CONECT   28   13                                                            
CONECT   29    5                                                            
CONECT   30    2                                                            
CONECT   31    8                                                            
CONECT   32   17                                                            
CONECT   33    4                                                            
CONECT   34    9                                                            
CONECT   35   11                                                            
CONECT   36   10                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12,26-tetrol	ChEBI
3alpha,7alpha,12alpha,26-Tetrahydroxy-5beta-cholestane	ChEBI
5beta-Cholestane 3alpha,7alpha,12alpha,27-tetrol	ChEBI
5beta-Cholestane-3alpha,7alpha,12alpha,26-tetraol	ChEBI
Cholestane-3,7,12,26(27)-tetrol	ChEBI
Cholestane-3,7,12,26-tetrol	ChEBI
Cholestane-3,7,12,27-tetrol	ChEBI
5beta-Cholestane-3alpha,7alpha,12alpha,26-tetrol	Kegg
(3a,5b,7a,12a)-Cholestane-3,7,12,26-tetrol	Generator
(3Α,5β,7α,12α)-cholestane-3,7,12,26-tetrol	Generator
3a,7a,12a,26-Tetrahydroxy-5b-cholestane	Generator
3Α,7α,12α,26-tetrahydroxy-5β-cholestane	Generator
5b-Cholestane 3a,7a,12a,27-tetrol	Generator
5Β-cholestane 3α,7α,12α,27-tetrol	Generator
5b-Cholestane-3a,7a,12a,26-tetraol	Generator
5Β-cholestane-3α,7α,12α,26-tetraol	Generator
5b-Cholestane-3a,7a,12a,26-tetrol	Generator
5Β-cholestane-3α,7α,12α,26-tetrol	Generator
(25R)-5-beta-Cholestane-3-alpha,7-alpha,12-alpha,26-tetraol	HMDB
5-b-Cholestane-3a-7-tetraol	HMDB
5-beta-Cholestane-3-alpha-7-alpha-12-alpha-26-tetraol	HMDB
5-beta-Cholestane-3a-7-tetraol	HMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27-tetraol	HMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27-tetrol	HMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27alpha-tetrol	HMDB
5 beta-Cholestane-3alpha,7alpha,12alpha,26-tetrol	HMDB
5-CTTL	HMDB
Cholestane-3,7,12,26-tetrol, (3alpha,5alpha,7alpha,12alpha)-isomer	HMDB

Chemical Formula

C₂₇H₄₈O₄

Average Mass

436.6676 Da

Monoisotopic Mass

436.35526 Da

IUPAC Name

(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol

Traditional Name

5-cttl

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO

InChI Identifier

InChI=1S/C27H48O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h16-25,28-31H,5-15H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

XJZGNVBLVFOSKJ-XZULNKEGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Tetrahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

26-hydroxysteroid
Tetrahydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Secondary alcohol
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-hydroxy steroid (CHEBI:17278 )
7alpha-hydroxy steroid (CHEBI:17278 )
12alpha-hydroxy steroid (CHEBI:17278 )
26-hydroxy steroid (CHEBI:17278 )
C27 bile acids, alcohols, and derivatives (C05446 )
C27 bile acids, alcohols, and derivatives (LMST04030014 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.77	ALOGPS
logP	3.62	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	17.42	ChemAxon
pKa (Strongest Basic)	-0.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	124.73 m³·mol⁻¹	ChemAxon
Polarizability	53.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon